β Scribed by Robin A. Fairhurst; Harry Heaney; George Papageorgiou; Robert F. Wilkins; Stephen C. Eyley
No coin nor oath required. For personal study only.
3-Methyl-1,3-oxazolidine and 3,4-dimethyl-5-phenyloxazolidine react with acidic reagents under aprotic conditions to afford reactive intermediates that interact with nucleophilic aromatic substrates and enolsilyl ethers to afford good yields of Mannich bases. Although 3-substituted-1,3-oxaxolidines' have been known for many years the only studies reported until recently have involved reactions with Grignard reagents. 2 The possibility of ring-chain tautomerism in the presence of acids has been studied recently by 1 H n,m.r. spectroscopy, 3 and hydroxy Schiff base -oxazolidine tautomerism has been discussed in terms of the apparent breakdown of Baldwin's rules. 4
The series of investigations by Griengl's group appears to be the only use in synthesis of these potentially interesting imonium ions.5
π SIMILAR VOLUMES
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The introduction of an aminomethyl substituent into aa indole nucleus by means of a Mannich condensation is well documented. 3 In